US20210238413A1 - Solid dispersion, preparation method therefor, chain-extended polyurethane using same, and epoxy resin composition comprising same - Google Patents

Solid dispersion, preparation method therefor, chain-extended polyurethane using same, and epoxy resin composition comprising same Download PDF

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Publication number
US20210238413A1
US20210238413A1 US17/054,286 US201917054286A US2021238413A1 US 20210238413 A1 US20210238413 A1 US 20210238413A1 US 201917054286 A US201917054286 A US 201917054286A US 2021238413 A1 US2021238413 A1 US 2021238413A1
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Prior art keywords
solid dispersion
dispersion
epoxy resin
dispersed
anhydride
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Inventor
Gwang Seok Song
Hoon Ryu
Jun Seop IM
Seung Hyun Yoo
Won Hyun JEON
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Samyang Corp
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Samyang Corp
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Priority claimed from KR1020180054295A external-priority patent/KR102129907B1/ko
Priority claimed from KR1020180057683A external-priority patent/KR102230451B1/ko
Priority claimed from KR1020180058790A external-priority patent/KR20190133865A/ko
Application filed by Samyang Corp filed Critical Samyang Corp
Assigned to SAMYANG CORPORATION reassignment SAMYANG CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: IM, JUN SEOP, JEON, WON HYUN, RYU, HOON, SONG, GWANG SEOK, YOO, SEUNG HYUN
Publication of US20210238413A1 publication Critical patent/US20210238413A1/en
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
    • C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
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    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
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    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/095—Oxygen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
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    • C08K5/00—Use of organic ingredients
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    • C08K5/00—Use of organic ingredients
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    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1535—Five-membered rings
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    • C08K5/00—Use of organic ingredients
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    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/08—Polyurethanes from polyethers
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/002—Inorganic compounds
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    • C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
    • C08J2301/02—Cellulose; Modified cellulose
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C08J2375/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2401/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
    • C08J2401/02—Cellulose; Modified cellulose
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    • C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/14—Polymer mixtures characterised by other features containing polymeric additives characterised by shape
    • C08L2205/16—Fibres; Fibrils
    • C—CHEMISTRY; METALLURGY
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    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines

Definitions

  • the present invention relates to a solid dispersion, a method for preparing the same, a chain-extended polyurethane using the same, and an epoxy resin composition comprising the same, and more specifically, to a solid dispersion which is possible to store and use easily, reduce transportation costs and prevent or improve the agglomeration and settling that occurs during product storage, enabling improved work efficiency, reduced process costs and improved strength when applied to polyurethane and providing improved strength compared to conventional curing agents by using an isotropic and/or anisotropic material derived from inorganic or organic material as a dispersoid and dispersing it in a dispersion medium such as polyol and sugar, which is solid at room temperature, a method for preparing the same, a chain-extended polyurethane using the same, and an epoxy resin composition comprising the same.
  • Isotropic and/or anisotropic materials derived from inorganic or organic materials are used as a main material in applications such as lightweight materials, hybrid materials, surface protectors, conductive pastes, conductive inks, sensors, precision analysis devices, optical memories, liquid crystal display devices, nanomagnets, thermoelectric media, high-performance catalysts for fuel cells, organic solar cells, nanoglass devices, abrasives, drug carriers, environmental catalysts, paints, printing inks, inkjet inks, resists for color filters, ink for writing tools and the like.
  • the isotropic and/or anisotropic materials derived from inorganic or organic materials are used industrially as a material that contributes to improved processing properties and product properties, quality stabilization and yield improvement during manufacturing by preparing and using a dispersion comprising them as fine particles in an aqueous dispersion medium or a non-aqueous dispersion medium.
  • dispersoid may agglomerate or settle in a short time in the dispersion medium.
  • the problems of aggregation and settling of dispersoids lead to a decrease in productivity, processing properties, handling properties and product yield, as well as a decrease in properties, material properties and quality of the final product in the manufacture of a dispersion.
  • it is known to cause undesirable phenomena such as decrease in transparency, gloss and coloring power, color stains and cracks in appearance.
  • a dispersant is used to suppress aggregation and settling of such dispersoids and to achieve dispersion stabilization.
  • the biggest problem with existing dispersion compositions is that when a dispersion composition using water as a dispersion medium is applied to polyurethane resins and epoxy resins, the process of manufacturing a master batch of water and polyol or a master batch of water and epoxy is additionally required and that a surfactant is needed to prevent agglomeration of dispersoids.
  • the purpose of the present invention is to provide a solid dispersion which is possible to store and use easily, reduce transportation costs and prevent or improve the agglomeration and settling that occurs during product storage, enabling improved work efficiency, reduced process costs, improved strength when applied to polyurethane and providing improved strength compared to conventional curing agents by using an isotropic and/or anisotropic material derived from inorganic or organic material as a dispersoid and dispersing it in a dispersion medium such as polyol and sugar, which is solid at room temperature, a method for preparing the same, a chain-extended polyurethane using the same, and an epoxy resin composition comprising the same.
  • the present invention provides a solid dispersion comprising a dispersoid and a dispersion medium in which the dispersoid is dispersed, wherein the dispersoid is an organic particle, an inorganic particle or a mixture thereof, and the dispersion medium is a non-aqueous dispersion medium in a solid state at room temperature.
  • the present invention provides a dispersion composition comprising the above solid dispersion.
  • the present invention provides a method for preparing a solid dispersion comprising a step of mixing a dispersoid and a dispersion medium; and a step of melting the dispersion medium in a mixture, wherein the dispersoid is an organic particle, an inorganic particle or a mixture thereof, and the dispersion medium is a non-aqueous dispersion medium in a solid state at room temperature.
  • the present invention provides a chain-extended polyurethane, which is prepared by the reaction of a polyurethane prepolymer and the above solid dispersion.
  • the present invention provides a method for preparing a chain-extended polyurethane comprising (1) a step of adding the above solid dispersion to the polyurethane prepolymer; and (2) a step of reacting the resulting mixture of step (1).
  • the present invention provides an epoxy resin composition comprising an epoxy resin; and the above solid dispersion.
  • the present invention provides a method for preparing an epoxy resin composition comprising a step of mixing the epoxy resin and the above solid dispersion.
  • the present invention provides a cured product obtained by curing the above epoxy resin composition.
  • the present invention provides a molded article comprising the above cured product.
  • the solid dispersion according to the present invention in which isotropic and/or anisotropic materials derived from inorganic or organic materials are dispersed can reduce or eliminate agglomeration during product storage, thereby reducing process input time when using a product (solid dispersion), reducing or eliminating an additional process or time for re-dispersing the agglomerated product and improving work efficiency since there is little or no concern for the worker's labor and safety during such additional process.
  • the solid dispersion of the present invention is evenly dispersed in a large amount of dispersoid, and when it is used as a chain extender for polyurethane, it is possible to provide improved strength to polyurethane as compared to a conventional chain extender. When it is used as a curing agent, improved strength compared to a conventional curing agent can be provided to the cured product of the epoxy resin.
  • the present invention relates to a solid dispersion comprising a dispersoid and a dispersion medium in which the dispersoid is dispersed, wherein the dispersoid is an organic particle, an inorganic particle or a mixture thereof, and the dispersion medium is a non-aqueous dispersion medium in a solid state at room temperature.
  • the present invention provides a dispersion composition comprising the above solid dispersion.
  • the solid dispersion or dispersion composition of the present invention may be solid at room temperature.
  • room temperature is a normal temperature in the range of 20 ⁇ 5° C., and may be, for example, 25° C.
  • the solid dispersion of the present invention may be used as a solid dispersion at room temperature for chain extension or a solid dispersion at room temperature for curing.
  • the solid dispersion of the present invention comprises a dispersoid dispersed in a dispersion medium.
  • the dispersoid comprised in the solid dispersion may play a role of improving electrical properties, thermal properties, and/or mechanical properties of the prepared polymer or cured product (for example, a polyurethane or an epoxy cured product) according to its type, but it is not limited thereto.
  • the dispersoid particles dispersed in the dispersion medium of the present invention may be selected from an inorganic particle, an organic particle or mixtures thereof.
  • the inorganic particles may be coated with a protective agent such as alkanic acids, fatty acids, hydroxycarboxylic acids, alicyclic carboxylic acids, aromatic carboxylic acids, alkenyl succinic anhydrides, thiols, phenol derivatives, amines, amphiphilic polymers, high-molecular-weight surfactants, and low-molecular-weight surfactants, etc.
  • a protective agent such as alkanic acids, fatty acids, hydroxycarboxylic acids, alicyclic carboxylic acids, aromatic carboxylic acids, alkenyl succinic anhydrides, thiols, phenol derivatives, amines, amphiphilic polymers, high-molecular-weight surfactants, and low-molecular-weight surfactants, etc.
  • organic pigments such as azo-based compounds, diazo-based compounds, condensed azo-based compounds, thioindigo-based compounds, indanthrone-based compounds, quinacridone-based compounds, anthraquinone-based compounds, benzimidazolone-based compounds, perylene-based compounds, phthalocyanine-based compounds, anthrapyridine-based compounds or dioxazine-based compounds; polymer resins such as polyethylene resin, polypropylene resin, polyester resin, nylon resin, polyamide resin, aramid resin, acrylic resin, vinylon resin, urethane resin, melamine resin, polystyrene resin, polylactic acid, acetate fiber, cellulose (for example, nanocellulose fibril, nanocellulose crystal, etc.), hemicellulose, lignin, chitin, chitosan, starch, polyacetal, polycarbonate, polyphenylene ether, polyether ether ketone, polyether ketone,
  • the dispersoid particles dispersed in the dispersion medium of the present invention may be crystalline or amorphous. Furthermore, the dispersoid particles dispersed in the dispersion medium of the present invention may be isotropic particles, anisotropic particles or fibrous particles.
  • the dispersoid particles dispersed in the dispersion medium of the present invention may be preferably one or more selected from the group consisting of nanocellulose fibrils, nanocellulose crystals, graphene, graphite, carbon nanotubes, carbon nanofibers, silver particles, silver nanowires, silver nanorods, gold particles, gold nanowires, gold nanorods, or a combination thereof, but they are not limited thereto.
  • the dispersoid particles may be obtained by a known method.
  • a method of preparing fine particles of dispersoids there are two kinds of a top-down method in which coarse particles are mechanically crushed and then refined, and a bottom-up method in which several unit particles are generated and are formed into particles through a cluster state in which they are aggregated. Even those prepared by any method can be preferably used.
  • a method for preparing the fine particles either a wet method or a dry method may be used.
  • the bottom-up method includes a physical method and a chemical method, but any method may be used.
  • a method of preparing metal nanoparticles among the dispersoid particles is exemplified.
  • the bottom-up methods as a representative example of the physical method, there is a gas evaporation method in which a bulk metal is evaporated in an inert gas and cooled and condensed by collision with the gas to generate nanoparticles.
  • a chemical method there is a liquid phase reduction method in which metal ions are reduced in the presence of a protective agent in a liquid phase, and the produced zero-valent metal is stabilized in a nano size, or a thermal decomposition method of a metal complex.
  • a chemical reduction method an electrochemical reduction method, a photoreduction method or a method in which a chemical reduction method and a light irradiation method are combined can be used.
  • the dispersoid particles that can be preferably used in the present invention may be obtained by any of a top-down method and a bottom-up method as described above, and may be prepared under any environment of an aqueous liquid phase, a non-aqueous liquid phase and a gas phase.
  • the solid dispersion of the present invention comprises a dispersion medium for dispersing a dispersoid.
  • the dispersion medium comprised in the solid dispersion When the dispersion medium comprised in the solid dispersion is applied to the production of polyurethane, it can play a role of extending the chain of the polyurethane, and when the dispersion medium comprised in the solid dispersion is applied to the curing of the epoxy resin, it can play a role of curing the epoxy resin.
  • the dispersion medium usable in the present invention may be a non-aqueous dispersion medium that is solid at room temperature but can change to a liquid state when the temperature is raised to a temperature exceeding room temperature.
  • a non-aqueous dispersion medium when the solid dispersion is stored at room temperature, dispersion stabilization can be achieved by preventing or improving the agglomeration or settling of the dispersoid.
  • the non-aqueous dispersion medium may be preferably one capable of extending the chain of polyurethane or curing the epoxy resin.
  • one or more selected from the group consisting of saccharides, polyether polyols, polyester polyols, hydrogenated sugars, alkane diols, amine-based compounds, phenol-based compounds, imidazole-based compounds, acid anhydride-based compounds, anhydrosugar alcohols or combinations thereof may be used.
  • Saccharides include monosaccharides, disaccharides, and polysaccharides, and the type of monosaccharide is not particularly limited. It can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature. For example, glucose, fructose, galactose, ribose or a mixture thereof may be used as the monosaccharide.
  • the type of the disaccharide is not particularly limited, and it can be used without limitation, as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature.
  • maltose, sucrose, lactose or a mixture thereof may be used as the disaccharide.
  • the type of the polysaccharide is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when heated above the melting point exceeding room temperature.
  • oligosaccharide, cellulose, starch, glycogen or a mixture thereof may be used as the polysaccharide.
  • the type of the polyether polyol is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature.
  • modified polypropylene glycol, polytetramethylene ether glycol (polytetrahydrofuran) or mixtures thereof and the like may be used as the polyether polyol.
  • the kind of the polyester polyol is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature.
  • butylene adipate diol, 1,6-hexane adipate diol or mixtures thereof and the like may be used as the polyester polyol.
  • the type of the hydrogenated sugar is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature.
  • tetritol, pentitol, hexitol, heptitol or a mixture thereof may be used as the hydrogenated sugar, and preferably hexitol such as one selected from the group consisting of sorbitol, mannitol, iditol, galactitol or a mixture thereof may be used.
  • the type of the alkanediol is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature.
  • one selected from the group consisting of 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol or a mixture thereof may be used as the alkanediol.
  • anhydrosugar alcohol e.g., monohydrosugar alcohol, dianhydrosugar alcohol or a mixture thereof
  • anhydrosugar alcohol e.g., monohydrosugar alcohol, dianhydrosugar alcohol or a mixture thereof
  • the type of the amine-based compound is not particularly limited, and can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature.
  • the kind of the phenol-based compound is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature.
  • one selected from the group consisting of 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, 3,5-xylenol, 2,5-dimethylphenol, 2,3-dimethylphenol or mixtures thereof may be used as the phenol-based compound.
  • the type of the imidazole-based compound is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature.
  • the kind of the acid anhydride-based compound is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature rises above the melting point exceeding room temperature.
  • the type of the monohydrosugar alcohol is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature is raised above the melting point exceeding room temperature.
  • one selected from the group consisting of tetritan, pentitan, hexitane, heptitan or a mixture thereof may be used as the monohydrosugar alcohol, and preferably hexitane such as one selected from the group consisting of sorbitan, mannitan, iditan, galactan or a mixture thereof may be used.
  • the type of the dianhydrosugar alcohol is not particularly limited, and it can be used without limitation as long as it is a solid at room temperature and is converted to a liquid state when the temperature rises above the melting point exceeding room temperature.
  • dianhydrosugar hexitol and the like may be used as the dianhydrosugar alcohol, and preferably one selected from the group consisting of isosorbide, isomannide, isoidide or mixtures thereof may be used.
  • the solid dispersion of the present invention when the solid dispersion of the present invention is a solid dispersion at room temperature for chain extension, one or more selected from the group consisting of anhydrosugar alcohol, hydrogenated sugar, alkane diol or a combination thereof may be used as the dispersion medium.
  • the solid dispersion of the present invention when the solid dispersion of the present invention is a solid dispersion at room temperature for curing, one or more selected from the group consisting of amine-based compounds, phenol-based compounds, imidazole-based compounds, acid anhydride-based compounds, anhydrosugar alcohols or a combination thereof may be used as a dispersion medium.
  • one or a mixture of two or more selected from anhydrosugar alcohols such as monohydrosugar alcohols and dianhydrosugar alcohols may be used.
  • the content of the dispersoid may vary depending on the type of dispersoid used and may be, based on 100 parts by weight of the dispersion medium, 0.0001 parts by weight or more, 0.01 parts by weight or more, 0.05 parts by weight or more, 0.1 parts by weight or more, 0.5 parts by weight or more or 1 part by weight or more, and 95 parts by weight or less, 90 parts by weight or less, 85 parts by weight or less, 80 parts by weight or less, 60 parts by weight or less, or 50 parts by weight or less—for example, 0.0001 parts by weight to 95 parts by weight, preferably 0.05 parts by weight to 80 parts by weight, but it is not limited thereto.
  • the content of the dispersoid is too small, the strength improvement of the polyurethane to which the solid dispersion is applied may be weak, and the physical and electrical properties due to the dispersoid effect in the epoxy resin cured product to which the solid dispersion is applied may be weak. If the content of the dispersoid is too much, it may not exist in a state that is evenly dispersed in the solid dispersion but may exist in a state where the dispersoids are tangled with each other.
  • the present invention provides a method for preparing a solid dispersion comprising a step of mixing a dispersoid and a dispersion medium; and a step of melting the dispersion medium in a mixture, wherein the dispersoid is an organic particle, an inorganic particle or a mixture thereof, and the dispersion medium is a non-aqueous dispersion medium in a solid state at room temperature.
  • the mixture in the step of melting the dispersion medium in a mixture, the mixture may be melted while removing moisture by applying a vacuum at a temperature equal to or higher than the melting point of the dispersion medium. Furthermore, the melted mixture may then be cooled to room temperature to obtain a solid dispersion.
  • the components described in the method for preparing the solid dispersion are the same as those of the above-described solid dispersion.
  • the present invention provides a method for preparing a chain-extended polyurethane comprising (1) a step of adding the solid dispersion according to the present invention to the polyurethane prepolymer; and (2) a step of reacting the resulting mixture of step (1).
  • the polyurethane prepolymer may be obtained by reacting a polyol and a polyisocyanate—for example, adding a polyol sufficiently vacuum-dried for 12 to 36 hours and polyisocyanate, preferably 20 to 28 hours, at 50 to 100° C., preferably 70 to 90° C. to a four-neck reactor and then reacting the polyol and polyisocyanate for 0.1 to 5 hours, preferably 0.5 to 2 hours while maintaining a temperature of 50 to 100° C., preferably 50 to 70° C. under a nitrogen atmosphere.
  • a polyisocyanate for example, adding a polyol sufficiently vacuum-dried for 12 to 36 hours and polyisocyanate, preferably 20 to 28 hours, at 50 to 100° C., preferably 70 to 90° C. to a four-neck reactor and then reacting the polyol and polyisocyanate for 0.1 to 5 hours, preferably 0.5 to 2 hours while maintaining a temperature of 50 to 100° C., preferably 50 to 70° C.
  • Polyols that can be used in the present invention are not particularly limited, but polyether polyols can be used.
  • polyether polyols can be used.
  • polyethylene glycol, polypropylene glycol, polytetramethylene glycol, random copolymers or block copolymers of ethylene oxide and propylene oxide, a random copolymer or a block copolymer of ethylene oxide and butylene oxide can be used.
  • the polyisocyanate compound usable in the present invention is not particularly limited, but specifically may be aromatic polyisocyanate compounds such as 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate (TDI), 2,6-tolylene diisocyanate, 4,4′-methylenediphenyl diisocyanate (MDI), 2,4-diphenylmethane diisocyanate, 4,4′-diisocyanato biphenyl, 3,3′-dimethyl-4,4′-diisocyanato biphenyl, 3,3′-dimethyl-4,4′-diisocyanato diphenylmethane, 1,5-naphthylene diisocyanate, 4,4′,4′′-triphenylmethane triisocyanate, m-isocyanatophenylsulfonyl isocyanate and p-isocyanato phenyl
  • a chain-extended polyurethane of the present invention after adding a solid dispersion for chain extension to the polyurethane prepolymer, by putting them in a coated mold and curing for 10 to 30 hours, preferably 15 to 25 hours at a temperature of 80 to 200° C., preferably 100 to 150° C., a chain-extended polyurethane can be prepared.
  • the present invention provides a chain-extended polyurethane, which is prepared by the reaction of a polyurethane prepolymer and the above solid dispersion of the present invention.
  • each component described in the chain-extended polyurethane and the method for preparing thereof is the same as those of the above-described solid dispersion.
  • the present invention provides an epoxy resin composition comprising an epoxy resin; and the above solid dispersion.
  • the epoxy resin may be those selected from the group consisting of bisphenol A-epichlorohydrin resin, epoxy novolac resin, alicyclic epoxy resin, aliphatic epoxy resin, bicyclic epoxy resin, glycidyl ester type epoxy resin, brominated epoxy resin, bio-based epoxy resin, epoxidized soybean oil or a combination thereof, but it is not limited thereto.
  • the epoxy resin may be novolac-type epoxy resins such as phenol novolac-type epoxy resin and cresol novolac-type epoxy resin; bisphenol-type epoxy resins such as bisphenol A-type epoxy resin and bisphenol F-type epoxy resin; aromatic glycidylamine-type epoxy resins such as N,N-diglycidyl aniline, N,N-diglycidyl toluidine, diaminodiphenylmethane-type glycidylamine and aminophenol-type glycidylamine; hydroquinone-type epoxy resin; biphenyl-type epoxy resin; stilbene-type epoxy resin; triphenolmethane-type epoxy resin; triphenolpropane-type epoxy resin; alkyl-modified triphenolmethane-type epoxy resin; triazine nucleus-containing epoxy resin; dicyclopentadiene-modified phenol-type epoxy resin; naphthol-type epoxy resin; naphthalene-type epoxy resin; aralkyl-type
  • the epoxy resin may be selected from the group consisting of glycidyl ether having one epoxy group such as bisphenol F-type epoxy resin, cresol novolac-type epoxy resin, phenol novolac-type epoxy resin, biphenyl-type epoxy resin, stilbene-type epoxy resin, hydroquinone-type epoxy resin, naphthalene skeleton-type epoxy resin, tetraphenylolethane-type epoxy resin, diphenyl phosphate (DPP)-type epoxy resin, tris(hydroxyphenyl)methane-type epoxy resin, dicyclopentadienephenol-type epoxy resin, diglycidyl ether of bisphenol A ethylene oxide adduct, diglycidyl ether of bisphenol A propylene oxide adduct, diglycidyl ether of bisphenol A, phenyl glycidyl ether, cresyl glycidyl ether; nuclear-hydrogenated epoxy resins, which are nuclear-hydrogenated products of these epoxy
  • the content ratio of the epoxy resin and the solid dispersion may be the value that makes the equivalent ratio of the solid dispersion to the epoxy resin (the equivalent of the solid dispersion/the equivalent of the epoxy resin)—for example, in the range of 0.25 to 1.75, more specifically in the range of 0.75 to 1.25, and more specifically, in the range of 0.95 to 1.05.
  • the equivalent of the solid dispersion relative to the equivalent of the epoxy resin is too small, there may be a problem in that the mechanical strength decreases and the physical properties in terms of thermal and adhesive strength decrease.
  • the equivalent of the solid dispersion to the equivalent of the epoxy resin is excessive, there may be a problem in that physical properties are deteriorated in terms of mechanical, thermal and adhesive strength.
  • the epoxy resin composition of the present invention may further include a curing catalyst.
  • the curing catalyst usable in the present invention may be selected from the group consisting of amine compounds (e.g., tertiary amines) such as benzyldimethylamine, tris(dimethylaminomethyl)phenol and dimethylcyclohexylamine; imidazole compounds such as 1-cyanoethyl-2-ethyl-4-methylimidazole, 2-ethyl-4-methylimidazole and 1-benzyl-2-methylimidazole; organophosphorus compounds such as triphenylphosphine and triphenyl phosphite; quaternary phosphonium salts such as tetraphenylphosphonium bromide and tetra-n-butylphosphonium bromide; diazabicycloalkenes such as 1,8-diazabicyclo[5.4.0]undecene-7 and organic acid salts thereof; organometallic compounds such as zinc octylate, tin octy
  • the curing catalyst may be selected from the group consisting of an amine compound, an imidazole compound, an organophosphorus compound or a combination thereof.
  • the amount used may be 0.01 parts by weight to 1.0 parts by weight, more specifically 0.05 parts by weight to 0.5 parts by weight, even more specifically 0.08 parts by weight to 0.2 parts by weight based on 100 parts by weight of the total of the epoxy resin and the solid dispersion, but is not limited thereto. If the amount of the curing catalyst used is too small, the curing reaction of the epoxy resin may not proceed sufficiently, resulting in a problem of deteriorating mechanical and thermal properties. On the contrary, if the amount of the curing catalyst is too large, the curing reaction progresses slowly even while the epoxy resin composition is stored, so there may be a problem wherein the viscosity increases.
  • the epoxy resin composition of the present invention may further comprise one or more additive components commonly used in the epoxy resin composition, if necessary.
  • additive components for example, one selected from the group consisting of antioxidants, UV absorbers, fillers, resin modifiers, silane coupling agents, diluents, colorants, antifoaming agents, defoamers, dispersants, viscosity modifiers, gloss modifiers, wetting agents, conductivity imparting agents or a combination thereof can be used.
  • the antioxidant may be used to further improve the heat resistance stability of the resulting cured product, and is not particularly limited.
  • a phenol-based antioxidant dibutylhydroxytoluene, etc.
  • a sulfur-based antioxidant mercaptopropionic acid derivative, etc.
  • phosphorus-based antioxidants (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, etc.) or combinations thereof may be used.
  • the content of the antioxidant in the composition may be 0.01 to 10 parts by weight, 0.05 to 5 parts by weight or 0.1 to 3 parts by weight, based on 100 parts by weight of the total of the epoxy resin and the solid dispersion.
  • UV absorber for example, benzotriazole-based UV absorbers such as TINUBIN P and TINUVIN 234 manufactured by BASF Japan Ltd.; triazine UV absorbers such as TINUVIN 1577ED; a hindered amine UV absorber such as CHIMASSOLV 2020FDL or a combination thereof, may be used.
  • the content of the UV absorber in the composition may be 0.01 to 10 parts by weight, 0.05 to 5 parts by weight or 0.1 to 3 parts by weight, based on 100 parts by weight of the total of the epoxy resin and the solid dispersion.
  • the filler is used for the main purpose of improving the mechanical properties of the cured product by blending it with an epoxy resin or a curing agent. In general, as the amount of addition increases, the mechanical properties are improved.
  • Inorganic fillers include extenders such as talc, sand, silica, calcium carbonate and the like; reinforcing fillers such as mica, quartz and glass fiber; some having special uses such as quartz powder, graphite, alumina and aerosil (the purpose of imparting thixotropic properties); the metals such as of aluminum, aluminum oxide, iron, iron oxide, copper, etc.
  • Fine particles with a large unit surface area are used to impart thixotropy (which refers to having the property in which it is in a liquid state when flowing and a solid state when stationary to prevent the resin impregnated on a vertical surface by immersion or impregnated on a vertical surface from spilling or loss during curing) to the resin.
  • thixotropy which refers to having the property in which it is in a liquid state when flowing and a solid state when stationary to prevent the resin impregnated on a vertical surface by immersion or impregnated on a vertical surface from spilling or loss during curing
  • colloidal silica aserosil
  • bentonite-based clay is used.
  • the filler is not particularly limited.
  • it may be one selected from the group consisting of glass fiber, carbon fiber, titanium oxide, alumina, talc, mica, aluminum hydroxide or a combination thereof.
  • the content of the filler in the composition may be 0.01 to 80 parts by weight, 0.01 to 50 parts by weight or 0.1 to 20 parts by weight, based on 100 parts by weight of the total of the epoxy resin and the solid dispersion.
  • the resin modifier is not particularly limited.
  • it may be flexibility-imparting agents such as polypropylene glycidyl ether, polymeric fatty acid polyglycidyl ether, polypropylene glycol, urethane prepolymer, etc.
  • the content of the resin modifier in the composition may be 0.01 to 80 parts by weight, 0.01 to 50 parts by weight or 0.1 to 20 parts by weight, based on 100 parts by weight of the total of the epoxy resin and the solid dispersion.
  • the silane coupling agent is not particularly limited.
  • it may be chloropropyltrimethoxysilane, vinyl trichlorosilane, ⁇ -methacryloxypropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane or a combination thereof.
  • the content of the silane coupling agent in the composition may be 0.01 to 20 parts by weight, 0.05 to 10 parts by weight or 0.1 to 5 parts by weight, based on 100 parts by weight of the total of the epoxy resin and the solid dispersion.
  • the diluent is used for the main purpose of lowering the viscosity by adding it to an epoxy resin or a curing agent, which serves to improve flowability, defoaming property, improve penetration into parts and add effectively a filler during use.
  • Diluents generally do not volatilize unlike solvents and remain in the cured product upon curing the resin, and are classified into reactive and non-reactive diluents.
  • the reactive diluent has one or more epoxy groups and participates in the reaction to enter a crosslinked structure in the cured product, and the non-reactive diluent is only physically mixed and dispersed in the cured product.
  • Commonly used reactive diluents include butyl glycidyl ether (BGE), phenyl glycidyl ether (PGE), aliphatic glycidyl ether (C12-C14), modified-tert-carboxylic glycidyl ester and the like.
  • BGE butyl glycidyl ether
  • PGE phenyl glycidyl ether
  • C12-C14 aliphatic glycidyl ether
  • modified-tert-carboxylic glycidyl ester and the like.
  • Dibutylphthalate (DBP), dioctylphthalate (DOP), nonyl-phenol, hysol and the like are generally used as non-reactive diluents.
  • the diluent is not particularly limited, but, for example, n-butyl glycidyl ether, phenyl glycidyl ether, glycidyl methacrylate, vinylcyclohexene dioxide, diglycidyl aniline, glycerin triglycidyl ether or a combination thereof may be used.
  • the content of the diluent in the composition may be 0.01 to 80 parts by weight, 0.01 to 50 parts by weight or 0.1 to 20 parts by weight, based on 100 parts by weight of the total of the epoxy resin and the solid dispersion.
  • Pigments or dyes are used as colorants to add color to the resin.
  • coloring agents such as titanium dioxide, cadmium red, shining green, carbon black, chromium green, chromium yellow, navy blue and shining blue are used.
  • additives such as an antifoaming agent and a defoamer used for the purpose of removing bubbles from the resin, a dispersing agent to increase the dispersing effect between the resin and the pigment, a wetting agent to improve the adhesion between the epoxy resin and the material, and a viscosity modifier, a gloss modifier for controlling the gloss of a resin, an additive for improving adhesion, an additive for imparting electrical properties, etc. can be used.
  • the curing method of the epoxy resin composition of the present invention is not particularly limited, and for example, a conventionally known curing apparatus such as a closed curing furnace or a tunnel furnace capable of continuous curing can be used.
  • the heating method used for the curing is not particularly limited but may be performed by a conventionally known method such as hot air circulation, infrared heating, high frequency heating, etc.
  • Curing temperature and curing time may be in the range of 30 seconds to 10 hours at 80° C. to 250° C.
  • post-curing may be performed under the conditions of 120° C. to 180° C., 0.1 hour to 5 hours.
  • it may be cured under conditions of 150° C. to 250° C. and 30 seconds to 30 minutes.
  • the present invention provides a method for preparing an epoxy resin composition comprising a step of mixing the epoxy resin and the above solid dispersion.
  • the present invention provides a cured product obtained by curing the above epoxy resin composition.
  • the present invention provides a molded article comprising the above cured product.
  • Example 1-A1 Solid Dispersion Comprising Nanocellulose Fibrils and Anhydrosugar Alcohols
  • isosorbide (Samyang Corporation) and 100 g of an aqueous solution in which 1% by weight of nanocellulose fibrils were dispersed (KB101, Asia Nano Cellulose Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 80° C. which is equal to or higher than the melting point of isosorbide. Subsequently, the melted mixture was cooled to room temperature to prepare isosorbide in which nanocellulose fibrils were dispersed (solid dispersion).
  • Example 1-A2 Solid Dispersion Comprising Nanocellulose Fibrils and Hydrogenated Sugars
  • sorbitol 100 g of sorbitol (Samyang Corporation) and 100 g of an aqueous solution in which 1% by weight of nanocellulose fibrils were dispersed (KB101, Asia Nano Cellulose Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 100° C. which is equal to or higher than the melting point of sorbitol. Subsequently, the melted mixture was cooled to room temperature to prepare sorbitol in which nanocellulose fibrils were dispersed (solid dispersion).
  • Example 1-A3 Solid Dispersion Comprising Nanocellulose Fibrils and Alkane Diol
  • 1,4-butanediol 100 g of 1,4-butanediol (Sigma Aldrich) and 100 g of an aqueous solution in which 1% by weight of nanocellulose fibrils were dispersed (KB101, Asia Nano Cellulose Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 40° C. which is equal to or higher than the melting point of 1,4-butanediol. Subsequently, the melted mixture was cooled to room temperature to prepare 1,4-butanediol in which nanocellulose fibrils were dispersed (solid dispersion).
  • Example 1-A4 Solid Dispersion Comprising Graphene and Anhydrosugar Alcohol
  • Example 1-A5 Solid Dispersion Comprising Graphene and Hydrogenated Sugar
  • Example 1-A6 Solid Dispersion Comprising Graphene and Alkane Diol
  • 1,4-butanediol 100 g of 1,4-butanediol (Sigma Aldrich) and 100 g of an aqueous solution in which graphene was dispersed at 1.5 mg/mL (WDG, MExplorer Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 40° C. which is equal to or higher than the melting point of 1,4-butanediol. Subsequently, the melted mixture was cooled to room temperature to prepare 1,4-butanediol in which graphene was dispersed (solid dispersion).
  • Comparative Example 1-A1 Liquid Dispersion Comprising Nanocellulose Fibrils and Polypropylene Glycol
  • Comparative Example 1-A2 Liquid Dispersion Comprising Graphene and Polypropylene Glycol
  • Example 1-B1 Preparation of Polyurethane Using a Solid Dispersion Comprising Nanocellulose Fibrils and Anhydrosugar Alcohol
  • a polyurethane prepolymer was prepared by reacting the mixture for 1 hour while maintaining a temperature of 60° C. under a nitrogen atmosphere.
  • PTMEG poly(tetramethylene ether glycol)
  • MDI 4,4′-methylene diphenyl diisocyanate
  • Example 1-B2 Preparation of Polyurethane Using a Solid Dispersion Comprising Graphene and Anhydrosugar Alcohol
  • Example 1-B1 a chain-extended polyurethane was prepared in the same manner as in Example 1-B1.
  • Example 1-B3 Preparation of Polyurethane Using a Solid Dispersion Comprising Nanocellulose Fibrils and Alkane Diol
  • Example 1-B1 Except for using the dispersion prepared in Example 1-A3 (1,4-butanediol in which nanocellulose fibrils are dispersed) instead of the dispersion prepared in Example 1-A1 (isosorbide in which nanocellulose fibrils were dispersed) as a chain extender, a chain-extended polyurethane was prepared in the same manner as in Example 1-B1.
  • Example 1-B4 Preparation of Polyurethane Using a Solid Dispersion Comprising Graphene and Alkane Diol
  • Example 1-B1 Except for using the dispersion prepared in Example 1-A6 (1,4-butanediol in which graphene was dispersed) instead of the dispersion prepared in Example 1-A1 (isosorbide in which nanocellulose fibrils were dispersed) as a chain extender, a chain-extended polyurethane was prepared in the same manner as in Example 1-B1.
  • Example 1-B5 Preparation of Polyurethane Using a Solid Dispersion Containing Nanocellulose Fibrils and Hydrogenated Sugar
  • Example 1-B1 Except for using the dispersion prepared in Example 1-A2 (sorbitol in which nanocellulose fibrils were dispersed) instead of the dispersion prepared in Example 1-A1 (isosorbide in which nanocellulose fibrils were dispersed) as a chain extender, a chain-extended polyurethane was prepared in the same manner as in Example 1-B1.
  • Example 1-B6 Preparation of Polyurethane Using a Solid Dispersion Comprising Graphene and Hydrogenated Sugar
  • Example 1-B1 Except for using the dispersion prepared in Example 1-A5 (sorbitol in which graphene was dispersed) instead of the dispersion prepared in Example 1-A1 (isosorbide in which nanocellulose fibrils were dispersed) as a chain extender, a chain-extended polyurethane was prepared in the same manner as in Example 1-B1.
  • Example 1-B1 Except for using isosorbide instead of the dispersion prepared in Example 1-A1 (isosorbide in which nanocellulose fibrils were dispersed) as a chain extender, a chain-extended polyurethane was prepared in the same manner as in Example 1-B1.
  • Comparative Example 1-B4 Preparation of Polyurethane Using a Liquid Dispersion Comprising Nanocellulose Fibrils and Polypropylene Glycol
  • Comparative Example 1-B5 Preparation of Polyurethane Using a Liquid Dispersion Containing Graphene and Polypropylene Glycol
  • the dispersed state of the dispersoid is the same as that immediately after preparation of the dispersion composition.
  • the dispersed state of the dispersoid is a state in which small lumps are floating compared to immediately after preparation of the dispersion composition.
  • the dispersed state of the dispersoid is a state in which big lumps are floating compared to immediately after preparation of the dispersion composition.
  • the dispersoid is insoluble in water.
  • Specimens were prepared in the same manner as described in the method of evaluating redispersibility. Subsequently, each of the prepared specimens was stored at room temperature for 1 hour, and then the degree of aggregation and settling of the dispersoid was visually observed, and the results are shown in Table 1 below.
  • ⁇ A small amount of dispersoid agglomerates and settles.
  • the dispersion was present in a solid state at room temperature and the storage stability was excellent, so it was found that long-term storage was easy and redispersability was excellent.
  • Example 2-A1 Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Anhydrosugar Alcohol
  • isosorbide (Samyang Corporation) as a dispersion medium and 100 g of an aqueous solution in which 1% by weight of nanocellulose fibrils were dispersed (KB101, Asia Nano Cellulose Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 80° C. which is equal to or higher than the melting point of isosorbide. Subsequently, the melted mixture was cooled to room temperature to prepare isosorbide in which nanocellulose fibrils were dispersed (solid dispersion for curing).
  • Example 2-A2 Solid Dispersion for Curing Comprising Graphene and Anhydrosugar Alcohol
  • Example 2-A3 Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Amine-Based Compounds
  • Example 2-A4 Solid Dispersion for Curing Comprising Graphene and Amine-Based Compounds
  • Example 2-A5 Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Phenol-Based Compounds
  • Example 2-A6 Solid Dispersion for Curing Comprising Graphene and Phenol-Based Compounds
  • Example 2-A7 Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Imidazole-Based Compounds
  • Example 2-A8 Solid Dispersion for Curing Comprising Graphene and Imidazole-Based Compounds
  • Example 2-A9 Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Acid Anhydride-Based Compounds
  • maleic anhydride (Sigma Aldrich) as a dispersion medium and 100 g of an aqueous solution in which 1% by weight of nanocellulose fibrils were dispersed (KB101, Asia Nano Cellulose Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 80° C. which is equal to or higher than the melting point of maleic anhydride. Subsequently, the melted mixture was cooled to room temperature to prepare maleic anhydride in which nanocellulose fibrils were dispersed (solid dispersion for curing).
  • Example 2-A10 Solid Dispersion for Curing Comprising Graphene and Acid Anhydride-Based Compounds
  • Example 2-B1 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Anhydrosugar Alcohol
  • Diglycidyl ether of bisphenol A (DGEBA)-based bifunctional epoxy resin (YD-128, Kukdo Chemical, epoxy equivalent weight (EEW): 187 g/eq, 1 equivalent) and isosorbide (Samyang Corporation, hydroxy equivalent weight (HEW): 73 g/eq, 1 equivalent) in which the nanocellulose fibrils are dispersed, prepared in Example 2-A1 were mixed, and 0.1 parts by weight of N,N-dimethylbutylamine (DMBA, Sigma Aldrich) was added based on 100 parts by weight of the mixture as a catalyst to prepare an epoxy resin composition.
  • DGEBA bisphenol A
  • EW epoxy equivalent weight
  • HEW hydroxy equivalent weight
  • the epoxy resin composition was put into a mold coated with a teflon film and cured stepwise at 100° C. for 1 hour, 120° C. for 1 hour, 150° C. for 3 hours and 180° C. for 1 hour.
  • Example 2-B2 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Graphene and Anhydrosugar Alcohol
  • Example 2-A2 hydroxy equivalent weight (HEW): 73 g/eq, 1 equivalent) in which the graphene was dispersed, prepared in Example 2-A2 as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1
  • the epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • Example 2-B3 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Amine-Based Compounds
  • Example 2-A3 Except for using (1R,2R)—N,N′-dimethyl-1,2-diphenylethane-1,2-diamine in which the nanocellulose fibrils were dispersed, prepared in Example 2-A3, as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1, an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • Example 2-B4 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Graphene and Amine-Based Compounds
  • Example 2-A4 Except for using (1R,2R)—N,N′-dimethyl-1,2-diphenylethane-1,2-diamine in which the graphene was dispersed, prepared in Example 2-A4, as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1, an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • Example 2-B5 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Phenol-Based Compounds
  • Example 2-A5 Except for using 2,3-xylenol in which the nanocellulose fibrils were dispersed, prepared in Example 2-A5, as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1, an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • Example 2-B6 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Graphene and Phenol-Based Compounds
  • Example 2-A6 Except for using 2,3-xylenol in which the graphene was dispersed, prepared in Example 2-A6, as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1, an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • Example 2-B7 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Imidazole-Based Compounds
  • Example 2-A7 Except for using the imidazole in which nanocellulose fibrils were dispersed, prepared in Example 2-A7, as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1, an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • Example 2-B8 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Graphene and Imidazole-Based Compounds
  • Example 2-A8 Except for using the imidazole in which graphene was dispersed, prepared in Example 2-A8, as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1, an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • Example 2-B9 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Nanocellulose Fibrils and Acid Anhydride-Based Compounds
  • Example 2-A9 Except for using the maleic anhydride in which the nanocellulose fibrils were dispersed, prepared in Example 2-A9, as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1, an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • Example 2-B10 Preparation of an Epoxy Resin Composition Using a Solid Dispersion for Curing Comprising Graphene and Acid Anhydride-Based Compounds
  • Example 2-A10 Except for using the maleic anhydride in which graphene was dispersed, prepared in Example 2-A10, as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1, an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • Comparative Example 2-B1 Preparation of an Epoxy Resin Composition Using Anhydrosugar Alcohol as a Curing Agent
  • Example 2-A1 Except for using isosorbide (Samyang Corporation, hydroxyl equivalent weight (HEW): 73 g/eq, 1 equivalent) as a curing agent instead of the isosorbide in which the nanocellulose fibrils were dispersed, prepared in Example 2-A1, an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • isosorbide Semyang Corporation, hydroxyl equivalent weight (HEW): 73 g/eq, 1 equivalent
  • Comparative Example 2-B2 Preparation of an Epoxy Resin Composition Using Anhydrosugar Alcohol as a Curing Agent and Adding Separate Nanocellulose Fibrils
  • Diglycidyl ether of bisphenol A (DGEBA)-based bifunctional epoxy resin (YD-128, Kukdo Chemical, epoxy equivalent weight (EEW): 187 g/eq, 1 equivalent), isosorbide (Samyang Corporation, hydroxy equivalent weight (HEW): 73 g/eq, 1 equivalent) and 0.73 g of nanocellulose fibrils were mixed, and 0.1 parts by weight of N,N-dimethylbutylamine (DMBA, Sigma Aldrich) was added based on 100 parts by weight of the mixture as a catalyst to prepare an epoxy resin composition.
  • DGEBA bisphenol A
  • DMBA N,N-dimethylbutylamine
  • the epoxy resin composition was put into a mold coated with a teflon film and cured stepwise at 100° C. for 1 hour, 120° C. for 1 hour, 150° C. for 3 hours and 180° C. for 1 hour.
  • an epoxy resin composition was prepared in the same manner as in Comparative Example 2-B2 and then cured.
  • Comparative Example 2-B4 Preparation of an Epoxy Resin Composition Using a Curing Agent Comprising Nanocellulose Fibrils and Polypropylene Glycol
  • Example 2-A1 polypropylene glycol in which nanocellulose fibrils were dispersed
  • Example 2-A1 isosorbide in which nanocellulose fibrils were dispersed
  • Comparative Example 2-B5 Preparation of an Epoxy Resin Composition Using a Curing Agent Comprising Graphene and Polypropylene Glycol
  • Example 2-A2 polypropylene glycol in which graphene was dispersed
  • Example 2-A1 isosorbide in which nanocellulose fibrils were dispersed
  • an epoxy resin composition was prepared in the same manner as in Example 2-B1 and then cured.
  • the dispersed state of the dispersoid is the same as that immediately after preparation of the solid dispersion for curing.
  • the dispersed state of the dispersoid is a state in which small lumps are floating compared to immediately after preparation of the solid dispersion for curing.
  • the dispersed state of the dispersoid is a state in which big lumps are floating compared to immediately after preparation of the solid dispersion for curing.
  • the dispersoid is insoluble in water.
  • Specimens were prepared in the same manner as described in the method of evaluating redispersibility. Subsequently, each of the prepared specimens was stored at room temperature for 1 hour, and then the degree of aggregation and settling of the dispersoid was visually observed, and the results are shown in Table 3 below.
  • ⁇ A small amount of dispersoid agglomerates and settles.
  • the solid dispersion for curing was present in a solid state at room temperature and the storage stability was excellent, so it was found that long-term storage was easy and redispersability was excellent.
  • Comparative Example 2-B1 in which simply a dispersion medium (anhydrosugar alcohol) alone was used as a curing agent, the tensile stress was significantly inferior to those of the Examples.
  • Comparative Examples 2-B2 and 2-B3 in which a dispersion medium (anhydrosugar alcohol) alone was used as a curing agent while an additive (nanocellulose fibrils or graphene) was mixed without prior dispersion, the additive was not evenly dispersed and the tensile stress could not be measured due to the aggregation of the cured product of the epoxy resin composition to which the solid dispersions were applied.
  • Example 3-1 Dispersion Composition Comprising Nanocellulose Fibrils and Monosaccharides
  • Example 3-2 Dispersion Composition Comprising Nanocellulose Fibrils and Disaccharides
  • sucrose 100 g of sucrose (Samyang Corporation) and 100 g of an aqueous solution in which 1% by weight of nanocellulose fibrils were dispersed (KB101, Asia Nano Cellulose Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 190° C. which is equal to or higher than the melting point of sucrose. Subsequently, the melted mixture was cooled to room temperature to prepare sucrose in which nanocellulose fibrils were dispersed (solid dispersion composition).
  • Example 3-3 Dispersion Composition Comprising Nanocellulose Fibrils and Polysaccharides
  • Example 3-4 Dispersion Composition Comprising Nanocellulose Fibrils and Anhydrosugar Alcohol
  • isosorbide (Samyang Corporation) and 100 g of an aqueous solution in which 1% by weight of nanocellulose fibrils were dispersed (KB101, Asia Nano Cellulose Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 80° C. which is equal to or higher than the melting point of isosorbide. Subsequently, the melted mixture was cooled to room temperature to prepare isosorbide in which nanocellulose fibrils were dispersed (solid dispersion composition).
  • Example 3-5 Dispersion Composition Comprising Nanocellulose Fibrils and Hydrogenated Sugars
  • sorbitol 100 g of sorbitol (Samyang Corporation) and 100 g of an aqueous solution in which 1% by weight of nanocellulose fibrils were dispersed (KB101, Asia Nano Cellulose Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 100° C. which is equal to or higher than the melting point of sorbitol. Subsequently, the melted mixture was cooled to room temperature to prepare sorbitol in which nanocellulose fibrils were dispersed (solid dispersion composition).
  • Example 3-6 Dispersion Composition Comprising Nanocellulose Fibrils and Polyether Polyol
  • Example 3-7 Dispersion Composition Comprising Graphene and Monosaccharide
  • Example 3-8 Dispersion Composition Comprising Graphene and Disaccharide
  • sucrose 100 g of sucrose (Samyang Corporation) and 100 g of an aqueous solution in which the graphene was dispersed at 1.5 mg/mL (WDG, MExplorer Co., Ltd.) were added to a rotary evaporator and uniformly mixed. Then, the mixture was melted while removing moisture by applying a vacuum under a temperature condition of 190° C. which is equal to or higher than the melting point of sucrose. Subsequently, the melted mixture was cooled to room temperature to prepare sucrose in which graphene was dispersed (solid dispersion composition).
  • WDG MExplorer Co., Ltd.
  • Example 3-9 Dispersion Composition Comprising Graphene and Polysaccharide
  • Example 3-10 Dispersion Composition Comprising Graphene and Anhydrosugar Alcohol
  • Example 3-11 Dispersion Composition Comprising Graphene and Hydrogenated Sugar
  • Example 3-12 Dispersion Composition Comprising Graphene and Polyether Polyol
  • Comparative Example 3-1 Dispersion Composition Comprising Nanocellulose Fibrils and Polypropylene Glycol
  • Comparative Example 3-2 Dispersion Composition Comprising Graphene and Polypropylene Glycol
  • the dispersed state of the dispersoid is the same as that immediately after preparation of the dispersion composition.
  • the dispersed state of the dispersoid is a state in which small lumps are floating compared to immediately after preparation of the dispersion composition.
  • the dispersed state of the dispersoid is a state in which big lumps are floating compared to immediately after preparation of the dispersion composition.
  • the dispersoid is insoluble in water.
  • Specimens were prepared in the same manner as described in the method of evaluating redispersibility. Subsequently, each of the prepared specimens was stored at room temperature for 1 hour, and then the degree of aggregation and settling of the dispersoid was visually observed.
  • ⁇ A small amount of dispersoid agglomerates and settles.
  • the dispersion composition was present in a solid state at room temperature and the storage stability was excellent, so it was found that long-term storage was easy and redispersability was excellent.

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